NO842247L - Fremgangsmaate for fremstilling av 6-alfa-(aminometyl)penicillansyre-1,1-dioksyd og derivater derav - Google Patents

Fremgangsmaate for fremstilling av 6-alfa-(aminometyl)penicillansyre-1,1-dioksyd og derivater derav

Info

Publication number: NO842247L
Authority: NO; Norway
Prior art keywords: ethyl; ethoxycarbonyloxy; formula; acid; dioxide
Prior art date: 1983-06-06

Application number

NO842247A

Other languages

English (en)

Norwegian (no)

Inventor

Wayne Ernest Barth

Original Assignee

Pfizer

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1983-06-06

Filing date

1984-06-05

Publication date

1984-12-07

1984-06-05 Application filed by Pfizer filed Critical Pfizer

1984-12-07 Publication of NO842247L publication Critical patent/NO842247L/no

Links

238000000034 method Methods 0.000 title claims abstract description 35
238000002360 preparation method Methods 0.000 title abstract description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 4
150000001875 compounds Chemical class 0.000 claims description 51
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 13
238000007327 hydrogenolysis reaction Methods 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 10
150000004795 grignard reagents Chemical class 0.000 claims description 9
-1 pivaloyloxymethyl Chemical group 0.000 claims description 9
239000007818 Grignard reagent Substances 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
230000004962 physiological condition Effects 0.000 claims description 7
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims description 6
PZTOXIPENNTIEM-UHFFFAOYSA-N phenylmethoxycarbonylaminomethyl acetate Chemical compound CC(=O)OCNC(=O)OCC1=CC=CC=C1 PZTOXIPENNTIEM-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
125000005643 gamma-butyrolacton-4-yl group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
FKENQMMABCRJMK-RITPCOANSA-N sulbactam Chemical compound O=S1(=O)C(C)(C)[C@H](C(O)=O)N2C(=O)C[C@H]21 FKENQMMABCRJMK-RITPCOANSA-N 0.000 abstract description 7
230000002401 inhibitory effect Effects 0.000 abstract description 6
108090000204 Dipeptidase 1 Proteins 0.000 abstract 1
102000006635 beta-lactamase Human genes 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
239000000047 product Substances 0.000 description 27
150000002148 esters Chemical class 0.000 description 18
230000003115 biocidal effect Effects 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
239000000203 mixture Substances 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
230000000694 effects Effects 0.000 description 8
238000001727 in vivo Methods 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
230000000844 anti-bacterial effect Effects 0.000 description 6
239000003782 beta lactam antibiotic agent Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000012267 brine Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
229920006395 saturated elastomer Polymers 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
238000003756 stirring Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
229930182555 Penicillin Natural products 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000002091 cationic group Chemical group 0.000 description 4
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
238000011081 inoculation Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 3
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 3
229920001817 Agar Polymers 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000008272 agar Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
208000022362 bacterial infectious disease Diseases 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000004185 ester group Chemical group 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
244000005700 microbiome Species 0.000 description 3
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 3
229940049954 penicillin Drugs 0.000 description 3
OSORMYZMWHVFOZ-UHFFFAOYSA-N phenethyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCCC1=CC=CC=C1 OSORMYZMWHVFOZ-UHFFFAOYSA-N 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000007790 scraping Methods 0.000 description 3
238000010561 standard procedure Methods 0.000 description 3
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 2
238000007256 debromination reaction Methods 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000007912 intraperitoneal administration Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
231100000636 lethal dose Toxicity 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
230000035945 sensitivity Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000005406 washing Methods 0.000 description 2
NDQQRRVKUBPTHQ-QBIQUQHTSA-N (2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO NDQQRRVKUBPTHQ-QBIQUQHTSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical class O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
238000010171 animal model Methods 0.000 description 1
238000009635 antibiotic susceptibility testing Methods 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical class C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000036765 blood level Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000011575 calcium Chemical class 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000003974 emollient agent Substances 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
210000004051 gastric juice Anatomy 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000001802 infusion Methods 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Chemical class 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000003973 paint Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
150000002960 penicillins Chemical class 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000011591 potassium Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
238000004321 preservation Methods 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000004289 sodium hydrogen sulphite Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229960005256 sulbactam Drugs 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000010977 unit operation Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO842247A 1983-06-06 1984-06-05 Fremgangsmaate for fremstilling av 6-alfa-(aminometyl)penicillansyre-1,1-dioksyd og derivater derav NO842247L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/501,476 US4502990A (en)	1983-06-06	1983-06-06	Process for 6-(aminomethyl)penicillanic acid 1,1-dioxide and derivatives thereof

Publications (1)

Publication Number	Publication Date
NO842247L true NO842247L (no)	1984-12-07

Family

ID=23993716

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO842247A NO842247L (no)	1983-06-06	1984-06-05	Fremgangsmaate for fremstilling av 6-alfa-(aminometyl)penicillansyre-1,1-dioksyd og derivater derav

Country Status (21)

Country	Link
US (1)	US4502990A (de)
EP (1)	EP0128718B1 (de)
JP (1)	JPS606692A (de)
KR (1)	KR870000313B1 (de)
AT (1)	ATE24513T1 (de)
AU (1)	AU545506B2 (de)
CA (1)	CA1209983A (de)
DE (1)	DE3461801D1 (de)
DK (1)	DK275984A (de)
ES (1)	ES8506317A1 (de)
FI (1)	FI842252A (de)
GR (1)	GR81626B (de)
HU (1)	HU191667B (de)
IL (1)	IL72002A (de)
NO (1)	NO842247L (de)
NZ (1)	NZ208380A (de)
PH (1)	PH19283A (de)
PL (1)	PL144041B1 (de)
PT (1)	PT78690A (de)
YU (1)	YU97184A (de)
ZA (1)	ZA844183B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4868296A (en) *	1985-10-29	1989-09-19	Pfizer Inc.	6-(1-carbamoyl-1-hydroxymethyl) penicillanic acid derivatives
US4797394A (en) *	1985-10-29	1989-01-10	Pfizer Inc.	6-(1-carbamoyl-1-hydroxymethyl)penicillanic acid derivatives

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4207323A (en) *	1975-11-21	1980-06-10	Merck & Co., Inc.	6-Substituted methyl penicillins, derivatives and analogues thereof
US4234579A (en) *	1977-06-07	1980-11-18	Pfizer Inc.	Penicillanic acid 1,1-dioxides as β-lactamase inhibitors
US4237051A (en) *	1979-04-19	1980-12-02	Schering Corporation	Stereospecific production of 6- or 7-carbon-substituted-β-lactams
US4309347A (en) *	1979-05-16	1982-01-05	Pfizer Inc.	Penicillanoyloxymethyl penicillanate 1,1,1',1'-tetraoxide
DE2927004A1 (de) *	1979-07-04	1981-05-27	Bayer Ag, 5090 Leverkusen	Penicillansaeure-1,1-dioxide, ihre herstellung und ihre verwendung als arzneimittel als arzneimittel
US4287181A (en) *	1979-10-22	1981-09-01	Pfizer Inc.	Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors
RO87705A (ro) *	1982-01-11	1985-10-31	Pfizer Inc,Us	Procedeu pentru prepararea unor derivati ai acidului 6-aminoalchilpenicilanic 1,1-dioxid

1983
- 1983-06-06 US US06/501,476 patent/US4502990A/en not_active Expired - Lifetime
1984
- 1984-06-04 EP EP84303733A patent/EP0128718B1/de not_active Expired
- 1984-06-04 AT AT84303733T patent/ATE24513T1/de not_active IP Right Cessation
- 1984-06-04 CA CA000455811A patent/CA1209983A/en not_active Expired
- 1984-06-04 PT PT78690A patent/PT78690A/pt unknown
- 1984-06-04 GR GR74909A patent/GR81626B/el unknown
- 1984-06-04 PL PL1984248045A patent/PL144041B1/pl unknown
- 1984-06-04 IL IL72002A patent/IL72002A/xx not_active IP Right Cessation
- 1984-06-04 DK DK275984A patent/DK275984A/da not_active Application Discontinuation
- 1984-06-04 DE DE8484303733T patent/DE3461801D1/de not_active Expired
- 1984-06-05 ES ES533148A patent/ES8506317A1/es not_active Expired
- 1984-06-05 PH PH30767A patent/PH19283A/en unknown
- 1984-06-05 YU YU00971/84A patent/YU97184A/xx unknown
- 1984-06-05 NO NO842247A patent/NO842247L/no unknown
- 1984-06-05 JP JP59115360A patent/JPS606692A/ja active Pending
- 1984-06-05 FI FI842252A patent/FI842252A/fi not_active Application Discontinuation
- 1984-06-05 ZA ZA844183A patent/ZA844183B/xx unknown
- 1984-06-05 HU HU842180A patent/HU191667B/hu unknown
- 1984-06-05 NZ NZ208380A patent/NZ208380A/en unknown
- 1984-06-05 KR KR1019840003123A patent/KR870000313B1/ko not_active IP Right Cessation
- 1984-06-05 AU AU29077/84A patent/AU545506B2/en not_active Ceased

Also Published As

Publication number	Publication date
PH19283A (en)	1986-03-04
PL144041B1 (en)	1988-04-30
KR870000313B1 (ko)	1987-02-26
PT78690A (en)	1984-07-01
DK275984D0 (da)	1984-06-04
DE3461801D1 (en)	1987-02-05
FI842252A0 (fi)	1984-06-05
JPS606692A (ja)	1985-01-14
KR850000447A (ko)	1985-02-27
ES533148A0 (es)	1985-07-01
HU191667B (en)	1987-03-30
GR81626B (de)	1984-12-11
DK275984A (da)	1984-12-07
IL72002A0 (en)	1984-10-31
AU2907784A (en)	1984-12-13
EP0128718B1 (de)	1986-12-30
NZ208380A (en)	1987-05-29
HUT34203A (en)	1985-02-28
US4502990A (en)	1985-03-05
YU97184A (en)	1986-06-30
ES8506317A1 (es)	1985-07-01
ZA844183B (en)	1986-01-29
ATE24513T1 (de)	1987-01-15
FI842252A (fi)	1984-12-07
AU545506B2 (en)	1985-07-18
IL72002A (en)	1988-03-31
EP0128718A1 (de)	1984-12-19
PL248045A1 (en)	1985-07-30
CA1209983A (en)	1986-08-19

Publication	Publication Date	Title
CA1178575A (en)	1984-11-27	Bis-esters of methanediol with acetonides of ampicillin or amoxicillin and penicillanic acid 1,1- dioxide
DE2824535B2 (de)	1980-05-14	Penkillansäure-l.l-dioxide, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DK150201B (da)	1987-01-05	Alfa-azido-n-acyl-6-aminopenicillansyreester til anvendelse ved fremstilling af den tilsvarende alfa-aminoforbindelse
US4155912A (en)	1979-05-22	2-Methylpenem-3-carboxylic acid antibiotics
EP0061313B1 (de)	1985-01-16	Bis-Ester von 1,1-Alkandiolen mit 6-beta-Hydroxymethylpenicillansäure 1,1-Dioxiden und beta-Lactam-Antibiotika
SU1556541A3 (ru)	1990-04-07	Способ получени фармацевтически приемлемых эфиров 7- @ -[2-(2-амино-4-тиазолил)-алкеноиламино]-3-цефем-4-карбоновой кислоты
CS228919B2 (en)	1984-05-14	Method of preparing halogenomethylester of 1,1-dioxide of penicillanic acid
FI82938C (fi)	1991-05-10	Foerfarande foer framstaellning av penicillansyraderivat med debromering.
NO842247L (no)	1984-12-07	Fremgangsmaate for fremstilling av 6-alfa-(aminometyl)penicillansyre-1,1-dioksyd og derivater derav
EP0040494B1 (de)	1984-02-15	Carbapename und Carbapen-2-Eme und ihre Herstellung
KR100257130B1 (ko)	2000-05-15	신규 세팔로스포린계 항생제 및 이의 제조방법
NO823093L (no)	1983-03-15	Fremgangsmaate for fremstilling av beta-laktamaseinhiberende forbindelser.
DK166883B1 (da)	1993-07-26	Analogifremgangsmaade til fremstilling af 6-aminoalkylpenicillansyre-1,1-dioxider samt derivater eller salte deraf
HU189917B (en)	1986-08-28	Process for producing 6-/2-amino-2-phenyl-acetamido/-penicillanic acid-/1,1-dioxo-penicillanoiloxi-methyl/-ester derivatives
NO832871L (no)	1983-06-23	Fremgangsmaate for fremstilling av penicillansyrederivater som er egnet som utgangsmateriale ved fremstilling av antibakterielle penicillinderivater
NO842249L (no)	1984-12-07	Fremgangsmaate for fremstilling av 6-(aminometyl)penicillansyre-1,1-dioksyd-estere
NO842248L (no)	1984-12-07	Fremgangsmaate for fremstilling av 6-aminometyl-penicillansyre-1,1-dioksyd-derivater
US4217274A (en)	1980-08-12	Methoxyethoxymethyl esters of penicillins
US4271172A (en)	1981-06-02	6-Amino-spiro[penam-2,4'-piperidine]-3-carboxylic acids, antibacterial compositions thereof and method of use thereof
CS255871B2 (en)	1988-03-15	Process for preparing derivatives of 6-/1-acyl-1-hydrohymethyl/-penicillanic acid
US4169833A (en)	1979-10-02	Novel phosphorane intermediates for use in preparing penem antibiotics
NO891403L (no)	1989-10-09	Nye forbindelser.
CA1101841A (en)	1981-05-26	Amino-spiro¬oxa(or thia) cycloalkane-penam\| - carboxylic acid derivatives
KR100229817B1 (ko)	1999-11-15	페넴 유도체 및 그의 제조방법
CN108727409A (zh)	2018-11-02	一种3-羟基头孢菌素的制备方法